Acetic Anhydride → HCID 59232150, compound

HRID 1091504Notes

Reaction equation

HRID 1091504 reaction equation
C(OC(=O)C)(=O)C.[C:8]([N:11]1[CH2:15][CH2:14][CH:13]([C:16]2[N:24]3[C:19]([C:20]([NH2:25])=[N:21][CH:22]=[N:23]3)=[C:18]([C:26]3[CH:31]=[CH:30][C:29]([NH:32][C:33]([NH:35][C:36]4[CH:41]=[C:40]([C:42]([F:45])([F:44])[F:43])[CH:39]=[CH:38][C:37]=4[F:46])=[O:34])=[C:28](F)[CH:27]=3)[CH:17]=2)[CH2:12]1)(=[O:10])[CH3:9]>>[C:8]([N:11]1[CH2:15][CH2:14][CH:13]([C:16]2[N:24]3[C:19]([C:20]([NH2:25])=[N:21][CH:22]=[N:23]3)=[C:18]([C:26]3[CH:27]=[CH:28][C:29]([NH:32][C:33]([NH:35][C:36]4[CH:41]=[C:40]([C:42]([F:45])([F:44])[F:43])[CH:39]=[CH:38][C:37]=4[F:46])=[O:34])=[CH:30][CH:31]=3)[CH:17]=2)[CH2:12]1)(=[O:10])[CH3:9]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 59232014HCID 59232014, compound

Product 1

HCID 59232150HCID 59232150, compoundYield 25%

Procedure

Example 206 (91 mg, 0.182 mmol) is allowed to react with acetic anhydride (20 mg, 0.200 mmol) following the procedure to make N-{4-[7-(1-acetylpyrrolidin-3-yl)-4-aminopyrrolo[2,1-f][1,2,4]triazin-5-yl]-2-fluorophenyl}-N′ [2-fluoro-5-(trifluoromethyl)-phenyl]urea. The product was purified by ether trituration to yield 25 mg (25%) pure desired product. 1H NMR (300 MHz, DMSO-d6) δ 10.12 (s, 1H), 10.05 (bs, 1H), 8.54 (d, J=5.1 Hz, 1H), 8.26 (t, J=8.4 Hz, 1H), 8.00 (s, 1H), 7.92 (s, 1H), 7.39 to 7.23 (m, 3H), 6.65 (d, J=4.5 Hz, 1H), 3.94 to 3.29 (m, 5H), 2.94 to 2.15 (m, 2H), 1.95 (s, 3H); MS [M+H]+=543.2; HPLC RT=2.66.

Workup

  1. customThe product was purified by ether trituration

Sources & evidence

ORD record
ord-c13751c32f7b4e80b50498092bb74e7a
Source dataset
uspto-grants-2012_03
Patent number
US08129379B2

Reaction notes

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